Holiday rentals with a kayak in Indian Shores

Townhouse in Redington Beach

A bright living area features comfortable white seating arranged around a wooden coffee table. Built-in shelves display books and decorative items. A flat-screen TV is mounted on a shiplap wall, while a dining area is visible in the background, showcasing a rustic table and modern fixtures.

Modern Townhouse right across beach! Table tennis

3 Bedroom/2.5 Bath modern townhome across street from beach, 2 large balconies off of living room and master bedroom. Lush landscaping. Enjoy meals in the beautiful dining area. Full equipped kitchen! Parking garage 1 car and driveway parking available. Sleeps 10. We rent all year round due to beautiful Florida weather. Walking distance to beach, restaurants, parks, basketball court, volleyball. Close to Johns Pass, 1 mile - Indian Rocks Beach. Tampa, Clearwater and St. Pete are a short drive.

LocationValueBarbecue

4.92 out of 5 average rating, 132 reviews

The exterior of a three-story building is presented, featuring multiple balconies with sliding glass doors. Lush greenery is visible in the foreground, framing a pathway leading to the entrance. The structure's design showcases natural materials and a coastal aesthetic.

4.9 out of 5 average rating, 147 reviews

On the Beach "Little Peace of Heaven" Beach Condo

Spacious - Complete Renovation - Come see!! Our building is on an Island and on the beach! Our unit faces East or the Inter-coastal but the beach is just downstairs. Our 8 unit building is ‘On the beach. Downstairs we have a beautiful semi-private patio area surrounded by sea grape plants. We have a table and chairs, 16 beach chairs, kayaks and paddleboards, outside shower, gas grill, & a firepit for all to enjoy. Wonderful & quiet for families & couples. No smoking in the unit. No pets.

Outdoor spacesLocationDecor

4.96 out of 5 average rating, 202 reviews

A private outdoor space features lush greenery framing a stone pathway leading to a wooden seating area. The area is adorned with tropical plants, creating a serene ambiance. A small bar-height table with stools is visible in the background.

Bungalow in Oldsmar

salt living at its best

- Resort Style Water front - Stand alone - Hot tub - Sunrise / sunset views on dock - free Kayaks - Internet / YouTube cable - 65” smart TV - Spacious Bedroom with king size bed, walk in closet and flat TV - Washer and Dryer in unit - Designated work space -Pet friendly - Fenced private patio - Free 2 cars / Boat Parking. - Central location ( beaches, restaurants, Tampa, St Pete’s, safety Harbor, Dunedin - 11 minutes from Ruth Eckerd event Hall - Pristine clean - Coffee station - Dining area

Outdoor spacesValueSleep quality

4.9 out of 5 average rating, 187 reviews

A welcoming living area features light-colored seating with orange and gray accents. A wooden coffee table is centered on a decorative rug. Natural light filters through the vertical blinds, illuminating the room's neutral tones, complemented by a potted plant and wall-mounted lighting.

Home in St. Petersburg

Hibernate in our Bear Creek Home

This 3 bedroom 2 bath home is located in beautiful Bear Creek. Don't worry, no bears! Great place to relax and enjoy the pool, in a quiet, safe neighborhood. Next to Pinellas Trail, a 40 mile paved trail. Great for walking, running and biking. You can bike downtown 6 mi or 4.6 miles to beaches. We have bikes and for those more adventuresome we have kayaks you may use. House features stable, high speed internet. Close to great restaurants, drugstores, supermarkets and coffee shops.

LocationValueAccuracy

Condo in Indian Rocks Beach

An aerial view captures the Aqua Beach Condo location, highlighting proximity to both the Intracoastal Waterway and the beach. Lush greenery and the vibrant blue waters contrast with the nearby buildings, while the sandy shoreline stretches along the coast under a clear sky.

Steps from the Sand - Clean, Stylish 2-BR Condo

AQUA BEACH CONDO - Only 90 steps from the beach, this beautifully updated and perfectly located beach condo offers you the very best of Indian Rocks Beach, a charming and intimate beach town located between Clearwater and St. Pete Beach. Two bedrooms with en-suite bathrooms and large walk-in closets, as well as the lofty living area and modern open kitchen will make you feel like at home. This condo is better equipped than your average vacation rental. Continue to read for more...

ValueOutdoor spacesBeach

4.95 out of 5 average rating, 231 reviews

A balcony view captures the sandy beach and turquoise waters, framed by lush greenery below. A few individuals can be seen enjoying the coastline, with palm trees providing shade. The clear blue sky complements the inviting seaside atmosphere.

4.9 out of 5 average rating, 165 reviews

Surfside Villas - Apartment B

Imagine waking up just steps from soft, sandy beaches and sparkling Gulf waters -- that's exactly what awaits at Surfside villas. Spectacular location right on Indian Shores Beach, you can stroll along the shore, watch stunning sunsets from your balcony, or simply unwind with the sound of the waves. Comfort & Convenience: The open-plan condo features a fully equipped kitchen, washer/dryer, and free on-site parking -- giving you all the comforts of home during your vacation.

Outdoor spacesValueFamily

4.97 out of 5 average rating, 143 reviews

Ocean Dreaming: Waterfront Home with Heated Pool,

Waterfront home: pool, dock, golf cart, kayaks, paddle board. This home has a private, zero-entry heated pool and dock (tie up your own boat or daily/weekly rental). 6-seat golf cart, 2-paddle boards, 2-sea kayaks, 6-bicycles and more are included. Two master bedroom suites with water views and soaking tubs plus a third bedroom with custom King Bed and Twin bunk beds. Two living areas are also each furnished with a queen sofa sleeper to accommodate a total of 12 people.

ValueLocationBackyard

4.89 out of 5 average rating, 165 reviews

Luxury waterfront | Walk to beach • Private dock

Welcome to Villa Azule, a spacious luxury waterfront retreat where the beach and boating lifestyle come together. Walk to Indian Rocks Beach in about 10 minutes, then return to your private waterfront setting with a dock, boat, and WaveRunner lifts. This 4-bedroom home sleeps up to 10 and includes complimentary kayaks, bikes, fishing and beach gear. With generous indoor-outdoor living and beautiful water views, Villa Azule is made for an unforgettable Florida getaway.

LocationValueTV

Bungalow in Indian Rocks Beach

A decorative lamp features a mermaid holding a round, glowing orb. The lamp is set against a backdrop of a colorful wave painting and neatly folded towels, adding a touch of coastal charm to the workspace.

Your private Waterfront Pool home!

Heated pool option added January 2026!! Waterfront property, perfect getaway for quiet relaxation or family fun. Come explore our gorgeous, resilient Gulf Coast:) Beach bungalow with all of the amenities. Have the house and pool with waterfront oasis all to yourself. Just step out the front door and walk 3 blocks to the sandy shores of Indian Rocks Beach. See hundreds of reviews to learn more about this host, our area, our style. BTR#1734 VRR#0422

ValueOutdoor spacesCheckout

4.97 out of 5 average rating, 233 reviews

4.93 out of 5 average rating, 147 reviews

Condo in Treasure Island

SolMate 2/2, kayaks, beach, views, boat slip

Newly renovated beach home, bright and beautifully appointed 2 bed/2 bath second floor condo with balcony overlooking Boca Ciega Bay. Modern beach decor. Only few steps to Treasure Island’s white sandy BEACH. Incredible water views from every window. 3 KAYAKS available (must sign waiver). Fun activities including ping pong, corn hole, etc. in common area. Only 6 units on property. Featured on HGTV Beachfront Bargain Hunt (Season 27 Episode 10).

ValueLocationBarbecue

A spacious living area features a comfortable brown sectional sofa adorned with patterned cushions. A round coffee table sits at the center. Natural light fills the room through large glass doors leading to a balcony. A cozy hanging chair and a dining area with bar stools are visible in the background.

4.92 out of 5 average rating, 126 reviews

Beautiful boho 2br townhome- pool, walk to beach!

Escape to comfort in this relaxing beach-style townhome, located in beautiful Indian Shores. This spacious townhome has all the amenities needed for a relaxing vacation for family, friends or a romantic getaway- just 2 min from beach access. Spacious renovated heated pool, and intercostal access for dolphin watching or kayaking ! Bike or walk to many shops and restaurants. The townhome is fully stocked so all you have to bring is yourself !

LocationValueAmenities

5.0 out of 5 average rating, 169 reviews

The grotto-style pool area features natural rock formations with cascading waterfalls and lush tropical plants. A hot tub is integrated into the design, providing a relaxing space. The serene water reflects the clear blue sky, while views of the bay are visible in the background.

Home in Oldsmar

Bayside Retreat your tropical oasis

"Bayside Retreat" is a Charming Private 1~bedroom/1 bath with full living room suite, located right on the water of upper Tampa Bay. Spend a quiet day lounging in the grotto pool, kayaking the bay, or a lazy day reading in the hammock. Enjoy breath taking sunrise and sunsets from the dock. Your own Tropical Paradise away from the rest of the world....... Just 15min to Raymond James Stadium. Centrally located 15 miles from TPA Airport

ValueLocationBreakfast

Popular amenities for Indian Shores kayak rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Holiday House Rentals with a Kayak

4.83 out of 5 average rating, 135 reviews

A spacious pool area features a heated saltwater pool and a hot tub surrounded by tropical landscaping. Lounge chairs are positioned nearby, and a grill is visible, providing an inviting outdoor space. The screened enclosure offers a sense of privacy and comfort.

Home in Belleair Bluffs

Hidden Oasis W Screened Heated Salt Pool / Hot Tub

ValueOutdoor spacesBeach

4.96 out of 5 average rating, 134 reviews

A serene outdoor space features a heated pool, reflecting the colorful sky during sunset. Strands of lights are draped above, enhancing the inviting atmosphere. Comfortable loungers are placed beside the pool, with dining areas visible in the background, surrounded by lush greenery.

Home in Dunedin

Heated saltwater pool|Spacious 4BR/3BA|

ValueOutdoor spacesHospitality

4.96 out of 5 average rating, 120 reviews

Home in St. Petersburg

Lux Mid-Century Downtown Courtyard+Parking

ValueLocationCheck-in

4.9 out of 5 average rating, 173 reviews

A charming farmhouse exterior is showcased under large trees, with a welcoming front porch featuring red seating and decorative plants. A spacious gravel parking area is visible, complemented by a green landscape in the background, enhancing the tranquil setting.

Home in Palm Harbor

Peaceful Pet friendly 2 BR cottage with hot tub.

Outdoor spacesLocationFamily

Home in Pass-a-Grille Beach

Steps 2 Beach- Cottage w/king bd +2bikes +parking

LocationValueTV

4.82 out of 5 average rating, 188 reviews

Superhost

Home in Redington Beach

Redington Beach near beach on ICW w/pool & dock

ValueOutdoor spacesSleep quality

4.9 out of 5 average rating, 10 reviews

4.95 out of 5 average rating, 19 reviews

Waterfront Luxury + heated pool + Golf Cart + Dock

Outdoor spacesLocationGetting around

A spacious living area features a large sectional sofa, complemented by decorative tables and potted plants. Expansive windows provide views of the water and outdoor seating, while natural light brightens the modern, open layout.

5.0 out of 5 average rating, 98 reviews

Walk to Beach! Waterfront Lux Retreat w/Kayaks

LocationValueAir conditioning

Other holiday rentals with a kayak

4.96 out of 5 average rating, 76 reviews

Oceanfront Condo with Beach Access

Outdoor spacesLocationLaundry

Apartment in Indian Shores

Spacious Beach Condo - Mariner's Pointe

ValueLocationComfort

5.0 out of 5 average rating, 52 reviews

Apartment in Indian Shores

Gulf-to-Bay Island Apt · Steps to Beach #1

LocationGetting aroundBarbecue

5.0 out of 5 average rating, 8 reviews

4.89 out of 5 average rating, 36 reviews

Fall special (reduced $+ min stay)-FL Gulf Coast

Outdoor spacesLocationWalkability

5.0 out of 5 average rating, 47 reviews

A spacious living area is furnished with a wraparound grey couch and two blue accent chairs. A round coffee table is centered in front, with a decorative bowl placed atop. Large windows allow natural light to fill the room and offer a view of the outdoor surroundings.

Condo in Madeira Beach

New Luxury 3BR Walk to Beach Pool, Spa + Parking

LocationOutdoor spacesCleanliness

4.73 out of 5 average rating, 26 reviews

Gulf Front Beauty 2BD 2BA w Bonus Room Sand Castle

ValueLocationKitchen

An open-concept living area features a comfortable sofa, a smart TV, and large windows showcasing views of the Intracoastal Waterway. A dining table for four pairs with additional seating, while a ceiling fan enhances airflow throughout the bright and airy space.

4.88 out of 5 average rating, 26 reviews

Intracoastal Views Condo | 3 min walk to beach!

ValueOutdoor spacesGetting around